Triethylamine → HCID 66632429, compound

To a stirred mixture of 1-(bromomethyl)-2-fluoro-3-nitrobenzene (0.70 g, 2.99 mmol) and dimethylamine hydrochloride (0.48 g, 5.98 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.91 g, 8.97 mmol) dropwise. The mixture was stirred at room temperature for 3 h and evaporated to dryness under reduced pressure. The residue was diluted with water (10 mL) and extracted with EtOAc (2×25 mL). The EtOAc solution was washed with water (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 1-(2-fluoro-3-nitrophenyl)-N,N-dimethylmethanamine (0.45 g, 76%) as a yellow viscous liquid. 1H NMR (400 MHz, CD3OD): δ 8.04-7.99 (m, 1H), 7.78-7.73 (m, 1H), 7.37 (td, 1H, J=8.0, 1.0 Hz), 3.64 (d, 2H, J=2.0 Hz), 2.29 (d, 6H, J=0.8 Hz).

1. customevaporated to dryness under reduced pressure
2. additionThe residue was diluted with water (10 mL)
3. extractionextracted with EtOAc (2×25 mL)
4. washThe EtOAc solution was washed with water (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customevaporated to dryness under reduced pressure
8. customThe residue was purified by MPLC on silica gel using
9. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-5558db3d026a42139fc6d62c2da96d95

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1